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以联苯和草酰氯为原料,通过傅克酰基化反应合成联苯-4-酮酸乙酯,经碱性水解得联苯-4-酮酸,在双氧水作用下,酮酸发生氧化脱羰基反应得目标产物。对酰化条件进行了优化并详细考察了氧化剂种类、双氧水浓度、物料配比、反应温度和时间对氧化脱羰基反应的影响,确定较佳的工艺条件:10%双氧水作氧化剂,n(联苯-4-酮酸)∶n(双氧水)=1∶2,反应时间为3 h,反应温度为0~5℃。在此条件下,联苯-4-甲酸的收率为81.9%(以原料联苯计),纯度为99.5%(HPLC面积归一化法)。产物结构经熔点、~1HNMR和~(13)CNMR和质谱表征。
Biphenyl and oxalyl chloride are used as raw materials to synthesize biphenyl-4-keto acid ethyl ester by Friedel-Crafts reaction. After basic hydrolysis, biphenyl-4-keto acid is generated. Under the action of hydrogen peroxide, keto acid undergoes oxidative decarbonylation The reaction of the target product. The conditions of acylation were optimized and the effects of oxidant species, hydrogen peroxide concentration, material ratio, reaction temperature and time on the oxidative decarbonylation were investigated in detail. The optimum conditions were as follows: 10% hydrogen peroxide as oxidant, n -4-ketoacid): n (hydrogen peroxide) = 1: 2, the reaction time is 3 h, the reaction temperature is 0 ~ 5 ℃. Under these conditions, the yield of biphenyl-4-carboxylic acid was 81.9% (based on the raw material biphenyl) and the purity was 99.5% (HPLC area normalization method). The product structure was characterized by melting point, ~ 1HNMR and ~ (13) CNMR and mass spectrometry.